Hydrochloric Acid → 5-Formylpyridine-2-carbonitrile

HRID 1747520Notes

Reaction equation

HRID 1747520 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:7]=[CH:8][C:9]([C:12]#[N:13])=[N:10][CH:11]=1.Cl.C(=O)(O)[O-].[Na+]>C1COCC1>[CH:2]([C:6]1[CH:7]=[CH:8][C:9]([C:12]#[N:13])=[N:10][CH:11]=1)=[O:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 586742865-(1,3-Dioxolan-2-yl)pyridine-2-carbonitrile

Product 1

HCID 109862635-Formylpyridine-2-carbonitrileYield 101.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In THF (5.0 mL) was dissolved 5-(1,3-dioxolan-2-yl)picolinonitrile (478 mg, 2.71 mmol) obtained in Step 2, and 1 mol/L hydrochloric acid (5.0 mL) was added under a nitrogen atmosphere at room temperature. The mixture was stirred at the same temperature for 16 hours and further stirred at 50° C. for 13 hours. The reaction mixture was neutralized with a saturated aqueous sodium bicarbonate solution. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure to give 5-formylpicolinonitrile (364 mg, 100% yield).

Workup

  1. additionwas added under a nitrogen atmosphere at room temperature
  2. stirringfurther stirred at 50° C. for 13 hours
  3. extractionExtraction with ethyl acetate
  4. washwashing with saturated brine
  5. dry with materialdrying over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. customthe solvent in the filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f010c44185b94ca18f505155ae5b3291
Source dataset
uspto-grants-2015_10
Patent number
US09150569B2

Reaction notes

Loading…